D-erythro-Eritadenine

Base Information

• Chemical Name: D-erythro-Eritadenine
• CAS No.: 23918-98-1
• Molecular Formula: C₉H₁₁N₅O₄
• Molecular Weight: 253.217
• Hs Code.: 2933990090
• Nikkaji Number: J611.458J
• Wikidata: Q104170965
• Metabolomics Workbench ID: 44107
• Mol file: 23918-98-1.mol

Synonyms:6-amino-alpha,beta-dihydroxy-9H-purine-9-butanoic acid;eritadenine;eritadenine, (R-(R*,S*))-isomer;eritadenine, (S-(R*,R*))-isomer;eritadenine, (S-(R*,S*))-isomer;eritadenine, monosodium salt, (R-(R*,R*))-isomer;eritadenine, monosodium salt, (S-(R*,R*))-isomer

Chemical Property of D-erythro-Eritadenine

Chemical Property:

• Vapor Pressure: 7.75E-22mmHg at 25°C
• Melting Point: >270°C (dec.)
• Refractive Index: 1.7610 (estimate)
• Boiling Point: 721℃
• Flash Point: 390℃
• PSA: 147.38000
• Density: 1.92
• LogP: -1.20390
• Storage Temp.: Refrigerator
• Solubility.: Aqueous Acid (Slightly, Heated), DMSO (Slightly)
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 253.08110385
• Heavy Atom Count: 18
• Complexity: 317

Purity/Quality:

98%Min ^*data from raw suppliers

Eritadenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)CC(C(C(=O)O)O)O)N
• Description: The empirical formula of this alkaloid should read C9H II N 504' The natural compound is the D-Erythro-form of the base. Melting points recorded for this alkaloid are 279°C (dec.) by Kamiya et al and 26l-3°C (dec.) by Chibata and his colleagues. The alkaloid has specific rotations of [α]D+ 16° (N-HC1) and [α] D + 50° (0.1 N-NaOH). It gives an ultraviolet spectrum in H20 with a single absorption maximum at 26l.5 nm which is shifted to 259.5 nm inN-HCl and is at 262 nm in N-NaOH. Eritadenine forms a methyl ester, m.p. 231°C (dec.) and a diacetate, m.p. 225°C (dec.).
• Uses: Hypocholesterolemic isolated from shiitake mushrooms, effecting phospholipid and linoleic acid metabolisms. Specifically, Eritadenine is a potent inhibitor of S-adenosyl-L-homocysteine hydrolase (SAHH), decreasing total cholesterol levels in plasma.

Technology Process of D-erythro-Eritadenine

There total 7 articles about D-erythro-Eritadenine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.5%

D-eritadenine ethyl ester (28987-93-1) → eritadenine (23918-98-1,25486-40-2)

Guidance literature:

With sodium hydroxide;

DOI:10.1135/cccc19821392

Reference yield:

5-(6-aminopurin-9H-9-yl)-5-deoxy-D-ribofuranoside (29789-09-1) → eritadenine (23918-98-1,25486-40-2)

Guidance literature:

With air;

DOI:10.1021/jf062559+

Reference yield:

methyl 5-(6-amino-purin-9-yl)-O2,O3-isopropylidene-D-5-deoxy-ribofuranoside (35910-49-7) → eritadenine (23918-98-1,25486-40-2)

Guidance literature:

Multi-step reaction with 2 steps

2: 95.5 percent / 0.05 M sodium hydroxide

With sodium hydroxide;

DOI:10.1135/cccc19821392

upstream raw materials:

D-eritadenine ethyl ester

methyl 5-(6-amino-purin-9-yl)-O²,O³-isopropylidene-D-5-deoxy-ribofuranoside

D-erythronolactone acetonide

adenine

Downstream raw materials:

(2R,3S)-erythro-9-(4-O-toluenesulfonyl-2,3-O-isopropylidene-2,3,4-trihydroxybutyl)adenine

Refernces

• 1、 Chibata,Okumura,Takeyama,Kotera. "Lentinacin: a new hypocholesterolemic substance in Lentinus edodes.". . p. 1237 - 1238. Retrieved 1969.
• 2、 Enman, Josefine,Rova, Ulrika,Berglund, Kris A.. "Quantification of the bioactive compound eritadenine in selected strains of shiitake mushroom (Lentinus edodes)". . p. 1177 - 1180. Retrieved 2007.